Looks like NW, so you have a few options:

1) Any of the beaches, but the best will be either Pass-A-Grille or Indian Rocks. PAG takes debit cards only, and IR is free parking if you find one of the little hidden public parking lots along the west side of the road. Read the signs closely...they look like no parking signs but they actually say between 6PM and 6AM or something like that.

Treasure island will also work and there is free parking and a HUGE beach for self launching (it's kite friendly), but it's not as good on a NW because of the current and slightly blocked beach from a North wind.

2) If you want flat water, you can ride backside skyway. If you are heading south to the skyway, it's the last exit before the skyway (it's the rest area)... follow it around to the right to the West side of the highway. There is a small (very small) launch surrounded by trees. Be careful, there is an oyster island straight out about 300 feet, but other than that it's all soft bottom, and grass flats as far as you can see on the other side of the channel.

Be careful not to end up down wind near the rest area itself because getting back is really difficult from that point.

As for when? I am guessing 2:30, but thats a guess not based on anything substantial other than my burning desire to ride.